Raising capital from family offices
Anomaly Deal Flow: How to Find and Attract Better Deals
Top 5 Strategic Investor Conversations in 2026 + 3 AI Developments to Watch
Capital raisers, sponsors and family office investors who want to judge deal quality and position themselves to see better deals first.
Five points worth keeping
- Deal flow is relative. A family office may review 30 deals a month or a week, while another investor sees 30 in three years. What counts as a top deal changes with how many deals the person sees.
- Aim for an anomaly deal. Richard says to look for deals three or four standard deviations from average. The deal should fit clear criteria such as structure, geography, team track record and a plan to grow value.
- Watch for the signs. People refer others before they invest. They say they have never seen it before, or ask how it works. Richard describes one single family office with a $150 million net worth that wanted to meet right away.
- Make it simple and visible. Investors rarely back what confuses them. Richard suggests meeting in person, showing the office, plant or properties, and making the deal easy to understand.
- Build a unique proposition. Many people can write a check, but fewer can open doors, help negotiate or make introductions. Exits, public listings and past deals with large investors help an investor stand out as a mentor.
Summary
Richard C. Wilson explains that a great deal depends on who is looking at it. An investor who sees 500 or 1,000 deals a year judges differently than one who sees 100. He also says having plenty of deal flow but too few investors is not a strong claim, since a site like LoopNet has more deal flow than investors.
He defines an anomaly deal as one three or four standard deviations from average. Signs include referrals before anyone invests, reactions like "I have never seen that before," and a structure that is simple to explain. He adds that positioning and a unique capital proposition draw better deal flow, and that a voicemail faces far less competition than an email.
Facts and figures
- Sophisticated investors may see 500 or 1,000 deals a year, which changes how they define a great deal.
- Richard describes a family office portfolio with three areas, and the offense area might use 5% of net worth to try for another 10, 50 or 100 million dollars.
- Richard says he receives 500 to 700 emails a day but only about 7 to 10 voicemails a day.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Top 5 Strategic Investor Conversations in 2026 + 3 AI Developments to Watch. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.
General education only. Not legal, tax or investment advice.
Worth quoting
"There are many people who can write a check. There are fewer people who can open doors, get distribution, help you negotiate a deal, make introductions."
"If you don't make things clear and simple, the subconscious read is that it's not for them."
"People don't invest in things that confuse them, typically."
Related questions
- Do family offices invest in funds or only direct deals?Family offices do both.
- What is the difference between single and multi-family offices?A single family office works for one family and is built the way that family wants.
- What deal sizes do family offices typically write?There is no single typical size.
Questions about this video
What is anomaly deal flow?
It is a deal that sits three or four standard deviations away from an average deal. Richard says it should look nothing like the other deals in an investor's inbox.
How can you tell you have a one in 500 deal?
People refer others to it before investing and say they have never seen it before. They also ask how it works or wish more deals had that structure.
Why does Richard prefer voicemail to email?
He says he gets about 7 to 10 voicemails a day but 500 to 700 emails a day. By those numbers, email is roughly 50 to 100 times more crowded than voicemail.
Put this into practice with the family office fit check. See all raising capital from family offices resources.
